Those Five Times (Destiel)
by Gemminycricket
Summary: The five times Dean wanted to kiss Castiel but didn't. (An inner monologue set in canon. Includes scenes direct from the show and lines direct from the script which I take no credit for)
1. The First Time

The first time Dean distinctly remembers wanting to kiss Castiel, was when he found him by the edge of the stream in Purgatory. Long before that, there had always been some kind of magnetism between them. The times they locked eyes for too long, the deep blue exploring the bright green. The times Dean found Cas standing a little too close—gradually Dean started to sense him before actually seeing him; he could feel the shift in the air, the subtle rise in temperature like another body radiating warmth.

But there was something else too. It was like a celestial energy.

Thinking back, Dean realised that that energy had always surrounded Cas like… well, like a halo, but the years had somehow intensified the angelic power. Like the time they spent together somehow nurtured it and made the sensation grow in strength. Which was strange to Dean, since he'd thought that familiarity would only weaken it, or at least make it easier to ignore; after all, you can get used to anything if you're around it for long enough.

Weirder still, however, was the fact that Sam apparently had no idea what he was talking about when Dean eventually felt the grudging need to bring it up after one particularly long visit from Castiel. The moment the angel disappeared with a faint flutter of his wings, the pages of their lore books flipping at the sudden breeze, Dean's shoulders loosened. He hadn't even noticed them tensing. He sheepishly rubbed the back of his neck, feeling the muscles in his biceps relax, and he wondered, horrified, that perhaps he had been flexing them.

Hell, he near blushed at the idea.

Diverting his gaze, as if disinterested in the very subject matter he was about to bring up, he asked Sam about the energy that came and left with Castiel.

"What do you mean?" Sam questioned. Dean could practically hear Sam's brow furrowing, confused not just at the context of the question but also at why Dean was asking in the first place.

"You know what I mean, Sam. It hangs around the guy like a bad smell," Dean retorted, opting not to mention how the energy was anything but bad. In fact, as it grew, so did Dean's liking of it. Were he to be honest, he'd admit how he'd actually started to miss it when it, and Cas, were gone; which occasionally were for long, uncomfortable periods of time.

"If you're talking about bad smells, Dean, then that was probably you. I don't think angels can pass gas," Sam said, only half sarcastic.

"Hey, no, _you_ are the gassy one," Dean can't help but be on the defence. He hadn't really wanted to have this conversation in the first place, and he regretted having it now that it was going just as badly as he'd expected. Really, he wished he hadn't brought it up at all. Dean hoped Sam would let it slide, but, like with most things, he was never that lucky.

"What does it feel like exactly? Added pressure in the atmosphere? Electrical charge?"

 _'_ _Damn,'_ Dean thought, _'Sam's actually giving it some consideration.'_ And only now did Dean realise just how indescribable the feeling truly was. It was everything Sam suggested and more, whilst being nothing like those things at all. Dean couldn't focus on any one distinguishing feature.

The fact that it kept intensifying didn't help him pin down the right definition for it, either.

All he knew was that it was there and it wouldn't go away and… hell, truth be told, he didn't want it to. All he understood was that it was distracting. It turned Castiel's presence into company with powerful baggage that, yes, sometimes actually made Dean weak at the knees.

And he never felt it in the vicinity of another angel. Uriel, Zachariah, Balthazar, even the freaking archangels, were all surrounded by nothingness. Were Dean to have simply walked by them unknowingly on the street, he wouldn't have felt a thing; they could have passed for humans.

But Cas? Cas was different.

"Look, never mind. Just forget I brought it up," Dean insisted with a dismissive wave of his hand.

"Dean—" Sam started.

"No. You were right, it's probably just me. All the sleep deprivation and the mass amount of burgers I eat that one stomach really shouldn't allow, it's got me all messed up. Even now I sense something radiating off you too… but it's less of an energy and more an annoying, droning noise."

Sam rolled his eyes and shook his head, finally allowing the subject to drop but Dean knew that his brother was still thinking about it. Pondering what his strange older brother was on about this time. It seemed that no matter how much time passed or many times he caught glimpses of the private life inside Dean's head, Sam could never truly understand him. Not all of him, anyway.

There was just so much that Dean kept to himself.

* * *

While Dean was in Purgatory, he'd hoped that the celestial energy would guide him to the missing angel, but the unfortunate truth was that Purgatory was just too big a place. Dean couldn't imagine where the monster pit started and where it ended, or whether it was just as infinite as the universe itself. In which case, he was surely walking in circles in what was quickly becoming a suicide mission to find Castiel—preferably alive.

He had noticed that time didn't pass there the same way it did on Earth. The light would filter away into an inescapable darkness unlike anything else Dean had seen before. For one thing, light was fickle; it didn't stick around long and whenever it decided to appear, it was dim at best, tainted by an ever-present layer of thick fog. In the minutes between night and day, the same fog would slowly roll downhill like an omen, signifying the onslaught of the pitch black nightfall. It would creep at Dean's ankles, concealing his way forward and evaporating the path back the way he came. Though, even it couldn't hide the eyes.

Dean swore there were eyes always watching him; not with a healthy curiosity but rather with ravenous, hostile intent. They would glow in the dark, blinking purposely and moving silently from one place to the next. They circled him constantly, biding their time, playing with their food before eating it. Whether they were vampires, werewolves, leviathans, or some other nasty creation, it simply didn't matter. They were all out for Dean's head and he knew that he was trapped there like Ripley on the ship in _Alien_ or the research crew in Antarctica with _The Thing_.

They were eventually going to kill him, it was just a matter of when. Until then, he'd keep going, refusing to go down without a fight. He couldn't give up even if he wanted to; Sam depended on him. Cas depended on him. Giving in now would be like handing them over to Death himself.

Now that Earth was free of the leviathans, Sam wouldn't be in any immediate danger, and sure, he could look after himself. But Dean couldn't help but wonder: _for how long?_

How long before something else came along, maybe something even worse? What could Sam's search for Dean bring down on humanity? After his trip to Hell pushed Sam straight into Ruby's manipulative hands, Dean worried what his disappearance would mean for his brother this time. Because he would try anything and everything to find him, never mind the risks, just the way Dean knew _he_ would were their roles reversed.

After all, that seemed to be where everything always went wrong. Dean selling his soul to Hell in exchange for his brother's life could arguably be where this whole mess started. Unwittingly breaking the first of the 66 seals, Lucifer being freed from the cage, Castiel's God rampage; it all seemed like dominoes falling into place, all leading him here to this hell adjacent nightmare.

Despite knowing this to be true, Dean still wouldn't change a thing. He couldn't even if he wanted to, but if changing the past meant burying Sam that night he was stabbed in the back, then Dean wouldn't even hear of it. Sam was alive, and that's all that mattered. And he knew that somehow, someway, he was going to find his way back to his little brother, and he was taking Cas with him.

That was of course, if he could even find the damn bastard in this shit storm.

* * *

The constant warfare was exhausting but Dean didn't dare rest his eyes even for a second. Though he certainly dreamed of what a couple hours sleep would feel like. He yearned for it. And it was quickly becoming a desperate situation. So finding Benny, or rather, being found by Benny, was like a godsend.

Dean didn't trust him at first, not by any means, but eventually trust didn't seem all that important anymore. He needed to rest, and Benny provided a set of eyes to keep watch so Dean could finally close his. The first time Dean woke up after a brief hour and a half of slumber and realised he was still miraculously alive, he decided this was an arrangement he could get on board with. The vampire would sit solemnly for an hour or two every couple of nights whilst Dean slept, guarding the vessel that would get him through the portal to the other side. It was a system that worked best for the both of them; the rest keeping Dean sharp and ready to fight.

Really, it kept them both alive.

If it weren't for that, then Dean may have considered battling on alone. In the time between kill or be killed, Benny felt the need to ask questions. Questions that Dean had no desire to answer. And it certainly started innocently enough: What's it like on Earth now? What has changed? What has stayed the same?

They were questions Dean allowed though he never went into much detail in his answers, as it was hard to describe what so often went by unnoticed—again, familiarity made everything very commonplace. But then when those questions ran out, Benny's curiosity focused more on Dean. More specifically: on the mysterious angel that he was dead-set on finding.

Dean wouldn't even give him the benefit of a response, which only fuelled Benny's intrigue and he would ask more and more questions, trying to wear the hunter down. And Dean honestly managed to hold his tongue for the longest time, eventually giving an actual answer entirely by accident rather than by choice.

"Look, I admit, I don't know a whole lot 'bout angels, but from what I've heard they ain't the most friendly of people," Benny contributed to their very one sided conversation, almost like he was talking to a brick wall.

"Yeah, well, Cas is different," Dean muttered, noncommittally.

"Cas, huh? What's that short for? Cassius? Casper? Cassie? Casey?"

Dean knew Benny would find a way to keep the list going on forever if he didn't give a straight answer. "Castiel. His name is Castiel."

"Or was," Benny pointed out with a casual shrug of his shoulders. "We've been looking for months, Dean. Perhaps your angel is long gone."

"Oh, you'd like that wouldn't you?" Dean bit back and gripped the handle of his blade tighter.

"Well, it would certainly get us out of this pit a whole lot quicker."

"You knew exactly what you signed up for," Dean said stiffly, "the angel comes with us or we don't go at all. If you have a problem with that, feel free to leave. I certainly won't try and stop you."

Benny held up his hands in surrender. "You're the boss. I just think you gotta face facts here, Dean…"

"No, you've got to shut your freaking pie hole before I shut it for you. Rather permanently, in a way I don't think you'd like. It would involve this blade separating your head from your shoulders. Understand?"

"I hear you, chief."

* * *

After that Benny never brought it up again, but it was clear that his patience was wearing thinner the further they went. To him each step felt like movement in the wrong direction, and every interrogation, he knew, was tedious. But he never complained. Not because of Dean's threat, but rather because he could see the utter desperation in the hunter's eyes, though Dean often tried to hide it.

Benny would stand aside as Dean would cut and tear into a werewolf or vampire, and he'd wait without argument until it was all done and dusted, and the creature's head was lying at Dean's feet, bleeding onto his shoes.

Without the answers he wanted to hear, Dean was obviously distraught, storming onward with a rage fuelled determination that quickly wavered and then he walked like an empty shell, hope abandoned. It was evident mostly in his shoulders that slumped forward, and in his hands that he compulsively clenched and unclenched, and Benny was starting to see the signs more and more often. He started to worry that maybe Dean would simply give up. After all, Dean had clearly said countless times that he wasn't leaving without Castiel, and he obviously meant it. Which could only mean one thing: Dean would die here.

Benny had survived just fine on his own, which was a strange thought since technically he was already dead. He didn't need Dean in order to live, not since he'd grown accustomed to the wild planes and the raw purity Purgatory maintained. Were Dean to die, Benny would continue on just as he had before, which really seemed like worse a fate than death. Sure it was pure, but Benny couldn't not resent it. There were things up top he needed to see, people he had unfinished business with, history he needed to bury. And he would be damned if Dean kept him from that. He was going to keep the hunter alive if it took everything he had, just as long as he got out. And if that meant finding the angel, well, then he'd find the angel.

"Dean, we can't be far off," Benny tried to sound optimistic, but it came across forced even to his own ears. "We'd know it if your angel were dead."

"I can't feel him," Dean admitted in a quiet, broken voice. "It's been months and I still can't feel him anywhere."

Benny didn't know what he meant, but he decided not to impose on whatever this breakdown was. "We'll find him."

"You don't get it, man. My brother's out there, back on Earth, and he needs me. The longer we're here in this shit stink, the closer he'll be to getting himself into some real nasty crap. But I can't leave without Cas, I owe him too much."

"There ain't nothin' your brother can do to crack into this locked box, Dean. He can't get himself into any trouble." Benny knew how much Dean worried about his brother, he'd heard the nightmares passing Dean's lips while he slept. "Look, we're getting outa here, one way or another. You've gotta get a grip."

Dean squared his shoulders and tensed his jaw, the dimness of his eyes bursting again with light. If he had to go down, he'd go down swinging. Like with most things, Dean pushed it all down; the inner turmoil he felt, the guilt, the anxiety. He suppressed it all and threw himself into the fight, actually seeking out something to kill rather than waiting for it to find him. And it helped. He didn't have to have any restraint here, he could just _go_ , and feel better for it when it was done. It gave him something else to think about.

Killing just came naturally to him, and eventually his fight turned into something almost manic. He was unstoppable. And it showed in his face each time he held the blade to a monster's throat, his eyes crazed with real, severe menace. He didn't have to say anything and the monsters just knew that he'd kill them, but not without making them hurt first. For most it would be a pain too intense to bear, and it hardly seemed worth the suffering when there was nothing actually worth living for.

* * *

"I don't think he knows, man," Benny muttered, loud enough for the werewolf to overhear. Sure, he could weasel the information out of the creature, but Dean could do it a lot quicker.

"Oh, he knows." Dean knelt down in front of the wolf, purposely placing the blade at the crook of his neck. The sharp edge served a very clear warning. "Where's the angel?"

Dean could recognise the fear in the mutt, could see as his chest started to rise and fall with much shorter breaths, and his lip quivered faintly. But there was something else there too. His eyes darted back and forth and then quickly diverted to peer just beyond Dean's face. The wolf knew something.

When he refused to meet Dean's piercing gaze, and his mouth didn't open to speak, Dean pressed the blade down harder against his skin.

"Hey!" Dean snapped, bringing the monster back to attention, forcing him into submission.

"There's a stream," the wolf finally divulged, hesitant in his answer. The blade was still cutting into his flesh.

"Go on."

"It runs through a clearing not far from here. I'll show you." He just needed time. Purgatory was an unforgiving place with flesh-tearing evils at every turn; which meant there was a chance, however slim, that he could escape their capture. Or better still, there was a chance that he could gain the upper hand and slaughter them both. And he would take his time with the hunter. After all, it was a hunter that got him there in the first place.

"How about you just tell me?" Dean suggested, bringing the demon-killing knife right to the underside of the wolf's chin.

The wolf swallowed hard and felt the sharp tip of the knife on his skin. As he tilted his head up, the blade followed. There wasn't a chance of him getting out of this alive. The hunter knew all the tricks in the book, knew what risks lied in trusting a werewolf. "Three days' journey. Follow the stream… There's a clearing. You'll find your angel there."

Dean was actually startled to be given an answer so easily, and pretended only momentarily to mull it over and purposely gave the creature the first glimmer of hope: he let the blade droop a little, the threat slowly retreating. Dean glanced back at Benny who raised an eyebrow, not willing to offer an argument for or against the oncoming slaughter. The vampire had become well-adjusted to Dean's gratuitously violent antics after spending the better half of a year with him. There was nothing Dean could do to surprise him anymore.

Dean turned his attention back to the werewolf, offering up a sadistic smile, "You know what, Mutt? ... I believe you."

He pierced upwards into the wolf's skull, the knife carving right through his tongue and into the roof of his mouth. The werewolf's eyes widened in shock, his mouth agape and blood filled the back of his throat, thin lines of red trickled down his chin. Benny saw his claws grasp handfuls of soil before, as he choked and gagged on his blood, his hands fell slack and the dirt slipped through his fingers.

The vampire silently dipped his head, shifting from one foot to the other. He wasn't opposed to killing, certainly couldn't afford to be around here, but he didn't exactly take pleasure in it either.

But Dean wasn't bothered. In fact, he looked pleased. The hunter stood upright and tugged the knife from the lifeless corpse, pausing to wipe the blade clean on the werewolf's filthy clothes.

"Let's get going then," he said, almost cheerily, and walked ahead. Benny stood back for only a moment before taking it in his stride, and following in the hunter's footsteps.

* * *

Dean's optimism grew exponentially after that, as if the very idea of seeing Castiel again renewed something within him that had become lost since first waking up in Purgatory. He was refreshed, his eyes alight with a new life and he walked eagerly ahead. The monsters kept coming but they hardly seemed a concern anymore, and Dean didn't find himself so desperate for the distraction. Killing them was work, nothing more; and Dean was still on his game: determined not to be delayed more than he needed to be.

And in those three days, Dean talked more than he had in months. Benny actually appreciated the light banter; it helped make the time pass quicker and helped him see the hunter more clearly. He'd known for a while that there was a whole lot of good in Dean, more than there was bad, but he hadn't realised just how free spirited he truly was. He had both the most immature and most mature sense of humour at the same time; laughing like an eight year old but usually at the dirtiest of jokes. And he was loyal. It was loyalty unlike anything Benny had ever encountered before.

Loyal through thick and thin and all the heartache and pain that came with it.

Benny finally got a sense of Dean's history with the mysterious angel, and whatever Dean didn't say in words, Benny understood in context. Even as he eased up, Dean seemed especially careful of what he said about Castiel. As if he was afraid Benny would think poorly of him before they actually got the chance to meet. And Benny noticed how Dean specifically darted around the topic of what exactly he thought or felt about Cas. His words were very on the nose recollections of how Cas gripped him tight and raised him from perdition, and how the angel had turned against heaven for Dean and the greater good, and how he stuck by the Winchester's through the apocalypse that the brother's, together, had started.

After that, Dean's tone noticeably dipped, and he grudgingly recalled Castiel's partnership with a demon named Crowley, and how he tried to become God, and how he released the leviathan into the world.

There was obviously a lot of bad blood buried there, but Dean had buried it deep. The truth was that he wanted, _needed_ , Cas. The angel had come into his life and there was just no taking him out of it. There was just so much good that couldn't be undone. Castiel's constant readiness to bleed for the Winchesters couldn't be overlooked—could never be tainted.

And to be honest, Dean felt a lot of the bad was his fault. Looking back on the whole life he had lived so far, he always dwelled on all that he felt he should have prevented or should have fixed: always thinking he should have said this or should have done that. Always: should've, would've, could've.

He had never had the chance to thank Castiel the way he wanted. Or to apologise as profusely as he knew he should. He tried so hard to remember in hindsight that while it was right in the ethical sense to fight against the God squad rather than alongside or for them, Cas was still fighting his family. _Family_. Dean didn't want to imagine what moral duress having to do that put Cas under.

Dean didn't want to remember how he had faced a fragmented-minded Castiel and told him: _"Nobody cares that you're broken."_

Nothing he said subsequently could ever take that back, and it too was something he wished he'd never said aloud. He realised only in retrospect that he often expected too much, grudged for too long, forgave too late, and yes, he selfishly took Castiel under his metaphorical wing and broke him.

And selfishly, he would do it again. Because he needed Cas. For more than his power; now he needed _him_. Dean needed that stupid trench coat and tie, he needed that familiar puzzled expression Cas often wore, and he needed that gruff voice and those striking blue eyes. He needed the way Cas made him feel.

All the months he spent searching for his angel, was time Dean spent hoping he'd never again be without him.

And as he drew nearer, he finally felt that energy in the air, the very celestial warmth Cas emitted, and Dean didn't even need to follow the stream anymore. He just followed his heart.

* * *

The longing to kiss Castiel came first when Dean saw him at the water's edge. The sensation was strong, the allure of Castiel's lips stunning Dean and his heart started to hammer in his chest. He just needed to be near Cas, touch Cas, hold Cas. He needed to embrace him and feel that he was really real.

"Cas!" Dean called out, his eyes locked on the angel that was crouched down by the water. Cas stood upright, his coat dirty and tattered, his chin coated with the beginnings of a beard. It was clear in the way he carried himself that Cas had gone through hell to get here alive.

Dean pulled the startled angel into a tight embrace, though he wanted more than anything to hold Castiel's face in his hands and kiss him long and hard on the lips. He wanted to tangle his fingers in Castiel's hair and pull him in close. He wanted to feel the angel's chest against his and have that energy as close as possible.

"Damn, it's good to see you," Dean breathed out, his hand clasping the back of Cas' coat.

He wanted to be with him every way he knew how.

But Purgatory wasn't the place. This wasn't the time. It was a boundary he had never crossed. And Benny was watching.

So instead of all that, he let the angel go and brushed his knuckles against Castiel's facial hair. "Nice peach fuzz."

"Thank you," Cas glanced back and forth between Benny and Dean, his posture stiff and he took tentative steps back as though contemplating making a run for it. Dean didn't seem to notice.

"You should meet somebody. This is Benny. Benny, this is Cas." Dean gestured to the vampire.

"Hola," Benny, however, did notice Castiel's body language and he wondered if the angel would actually dare zap away again, leaving Dean. Benny was wary of Cas and was carefully sizing him up, trying to find what made this angel worthy of saviour.

Cas turned his gaze back on the hunter, "How did you find me?" It almost sounded as if he meant; _'why did you find me?'_

"The bloody way," Dean allowed Cas to interpret that any way he wanted. "You feeling okay?"

"You mean am I still? ..." Cas twirled his finger in a circular motion at his ear, his expression serious.

"Yeah, if you want to be on the nose about it, sure," Dean chuckled lightly, appraising Castiel to try and see for himself what condition he was really in. From the outside he seemed more himself. He stood taller, looked sterner, and didn't so easily lose focus. He wasn't off chasing the bees. Dean took that to be a good sign.

"No, I'm perfectly sane. But then, 94% of psychotics think they're perfectly sane, so I guess we'd have to ask ourselves 'what is sane?'"

There it was. There was the man Dean knew. There was Castiel who so often said the strangest things at the best of times. There was Castiel who took into consideration everything that Dean too easily forgot or didn't think held any significance. There was Castiel, just the way Dean had always liked him.

"That's a good question," Dean granted.

"Why'd you bail on Dean?" Benny questioned, stepping forward to interrogate the angel. If Castiel was willing to fly off, then there was no time like the present.

"Dude…" Dean warned, not wanting to scare Castiel away.

"The way I hear it, you two hit monster land and hot wings here took off. I figure he owes you some backstory."

"Look, we were surrounded, okay? Some freak jumped Cas. Obviously, he kicked its ass, right?" Dean waited for Cas to back his story, but the faint fear he'd repressed came to the surface when the confirmation never came.

Castiel's eyes dipped with guilt, "No."

Dean's heart sank, but the need to kiss Castiel didn't fade. Instead the desperation became less that of a heated desire and more that of sadness. Now he wanted to hold onto the collar of Castiel's trench coat and never let go. He wanted to bury his face in the crook of Castiel's neck and close his eyes, hoping the angel wouldn't suddenly disappear beneath his hands. He wanted his lips to linger tenderly on Castiel's, a kiss that silently begged; _'please don't go'_.

But Purgatory wasn't the place. This wasn't the time. It was a boundary he had never crossed. And Benny was watching. That, and his angel just admitted to leaving Dean to fend for himself in the land inhabited exclusively by monsters. Dean didn't know what to do with this harsh truth.

"What?" Dean asked in disbelief.

"I ran away," Castiel locked eyes with Dean but there a quiet grief lingering in that intense blue gaze. His confession came from a heavy heart.

"You ran away?"

This was Castiel; the man that had, only months prior, looked at Dean and said; _"Well, I'll go with you. And I'll do my best",_ though knowing he was risking his own life in order to kill Dick Roman. Though it meant sacrificing the pacifism he had worked so hard to maintain. Though it meant facing all the mistakes he had made and the destruction he had caused. He had stood there, essentially staring into the barrel of a gun, and offered up his life. Because Dean had asked him to.

Dean couldn't believe that the man who had done that, could really be standing here now saying he had jumped ship and left Dean to sink alone.

"I had to," Castiel so clearly wanted Dean to understand. But Dean was struggling. Everything was starting to too closely resemble being betrayed the first time. And while he didn't want to believe it, it didn't put a stop to the voice in his head that said; _'what if it's true?'_

"That's your excuse for leaving me with those gorilla-wolves?"

"Dean—"

"You bailed out and, what, went camping? I prayed to you, Cas, every night," Dean was distraught.

He wasn't really one for prayer; it never sat right with him, always felt very false on his tongue. He avoided it where he could. But since losing Cas in Purgatory… well, truthfully, since long before that, back when Castiel descended into the lake never to emerge, Dean had prayed to him, for him, about him. He'd never told anyone about it, least of all Sam, knowing just how pathetic it really was. But he had been lonely. He had been without someone that mattered so dearly to him in a way no one else had. And prayer seemed like the last option he had to keep himself going, when even booze couldn't numb the pain.

"I know," Cas admitted quietly.

Now it all seemed foolish. Since apparently Castiel wouldn't go to him even when he was able to hear him. He'd listen to the begging and the suffering and do nothing.

"You knew, and you didn't—what the hell's wrong with you?" Dean couldn't keep the hurt out of his voice. He'd long ago worked up a narrative to explain Castiel's disappearance, and now that the truth didn't fit, he found it jarring. Upsetting. Like finding out Santa wasn't real, but worse.

Worse because this was Cas.

"I am an angel in a land of abominations. There have been things hunting me since the moment we arrived," Castiel explained.

"Join the club!" Dean fumed.

"These are not just monsters, Dean. They're leviathan. I have a price on my head, and I've been trying to stay one step ahead of them to… to keep them away from you. That's why I ran."

Dean lingered on the pause in Castiel's words, the second his voice softened and laid his emotions bare. He'd once again offered his life for Dean.

A dense silence hung between them, the only sound now that of the running stream, and the three of them tried to find the right words. Benny could see that Castiel was being sincere, but he believed the angel to be misguided, believed him to be someone that had a tendency to repeat history; recreate the same mistakes they had made many times before. Castiel, in his eyes, wasn't reliable.

"Just… leave me. Please," Castiel insisted, turning his gaze out to the horizon, but his attention was restless. He was forcing himself to turn away from Dean, knowing it was best for the hunter to continue on without him, but it would hurt him to watch Dean go all the same.

"Sounds like a plan," Benny jeered, happy to leave the angel behind, "let's roll."

"Hold on, hold on," Dean gestured for Benny to stop, and the vampire did so grudgingly. "Cas, we're getting out of here. We're going home." Dean wanted to step forward and caress Castiel's cheek, wanted him to look into his eyes and see just how desperately he wanted him. How much he needed him.

"Dean, I can't," Cas stared forlornly at the ground. If he were to look up, he'd give in. He always did in the end.

"You can. Benny, tell him."

"Purgatory has an escape hatch, but I got no idea if its angel friendly," Benny explained honestly, but he was hoping to convince the angel to stay behind. Castiel was dangerous cargo to carry, his grace shining like a beacon to all of Purgatory's monsters. He'd slow them down. Hell, they might not even make it with the angel attracting enemies like a magnet.

"We'll figure it out," Dean dismissed. The details didn't matter. "Cas, buddy, I need you."

"Dean…" Cas looked to Dean, unable to express in words everything he wanted to say.

"And if leviathan want to take a shot at us, let them. We ganked those bitches once before, we can do it again."

Cas shook his head faintly, "It's too dangerous."

"Let me bottom line it for you. I'm not leaving here without you. Understand?" Dean emphasized.

"I understand."

* * *

Dean wished he had seen it then. Wished he had heard it in Castiel's voice. The way he said it like a soldier taking on a duty. Cas understood perfectly. He knew that Dean wouldn't ever leave him behind, so he had no choice but to lead Dean to the portal to ensure the hunter's freedom.

Dean wished he had recognised the way Cas straightened his spine and broadened his chest, the way his eyes flickered with purpose. Maybe then Dean could have held on tighter and never allowed Cas to let go. He could have, should have, dragged the angel through the eye of the needle, and held him forever in his arms.

* * *

 **Thanks for reading, guys! I hoped you enjoyed the first of five chapters. I have never written Destiel before so I found writing in and around scenes direct from the show to be a good way to start. And I think in a way having this inner monologue helps justify the ship without taking away from canon. Please let me know what you thought :)**


	2. The Second Time

The second time Dean wanted to kiss Castiel was when the angel came back from Purgatory.

Dean had started to feel that energy again, and he tried so hard to ignore it. It felt heavy in his chest. It weighed down on him, because he thought it was just him longing for Castiel. Then, as it gradually grew stronger, he thought it was false hope; which was so much worse.

That's how it started; sensing his angel, and missing him even more than he thought possible. He'd fall quiet whenever the feeling came to him, as he tried equally to force it away and to take comfort in it. It gave the illusion that Cas must be there somewhere nearby. Which was really just a cruel trick for his mind to play on him.

It was taunting him, playing with his guilt.

Then Dean started to see him. He saw him by the side of the road, his coat tattered the way it had been in Purgatory. It was Cas the way he had seen him last, like no time had passed since. Dean slammed his foot on the brake and then reversed, turning to look out the rear windshield, but he couldn't see anything. The trees swayed lazily in the breeze, cicadas clicked faintly in the distance. It was just him and the open road. Dean pulled on the hand brake, got out of the Impala with the engine still running, and stood, lost, in the middle of the road, his heart hammering and his skin crawling—but the hope was spent. There was nothing, and no one, to see.

It was getting worse.

He felt locked in place for the longest time, leaning against the side of the Impala and he ran his hand down over his face, thinking perhaps he was just exhausted. It would certainly explain the hallucination, maybe even the feeling of Castiel's presence as well. He couldn't be blamed for what he couldn't control; the excuse was entirely reasonable.

And yet he still wasn't convinced.

With a forlorn shake of his head, he got back into the car and drove, the speedometer creeping over the speed limit with his thoughts elsewhere rather than on the road. It took all his strength to only look back once, and he wished he hadn't. It meant he'd given in to his delusions, having already been feeding them each time he even considered the possibility of Castiel's return.

After that, Cas was permanently in his thoughts. He started to wonder what must have happened to him, alone in Purgatory. He wondered how soon after the portal closed the angel would have been torn to shreds or completely consumed by the leviathan. He wondered if it had happened fast. He wondered what Castiel's last thoughts may have been, if they weren't those of all consuming fear—he wondered if they were at all about him.

Dean liked to think that Cas had put up a good fight; that he had made those last moments mean something, but the hard truth was that Cas was weak when Dean left him.

When Dean inadvertently abandoned him.

Cas wasn't strong enough to fend for himself for much longer—maybe he even died right there on that cliff.

Maybe Cas died right where Dean left him.

Dean experienced another pang of guilt at the very idea, and he couldn't get the image out of his head. He couldn't distract himself as completely as he wanted to. Castiel's lifeless body always came back to him, and he tried to repress his depression so Sam couldn't see it. There was nothing his brother could say or do to make it better, and he didn't want to confess what really happened at that portal.

He didn't want to describe to him the moment Castiel's hand slipped through his fingers. Didn't want to admit how Castiel had desperately called Dean's name, his hand clasping at the air as he tried to hold onto the hunter.

It didn't matter that Dean had tried his best. He found no solace in the thought. It didn't matter how it happened or how far he tried to reach out, because it didn't change anything. Dean was here, and Cas was there; probably dead. All those months without the angel did nothing to prepare him for this, it didn't make the loss any easier.

And that night, he saw Cas again, this time at the window, standing solemnly in the storm.

Dean approached the window with caution, and with a reserved hope, not wanting to be played the fool twice in one day. The lightning flickered again, casting brief bursts of light into the hotel room and it illuminated Dean's face. He felt emptier than he had in a long time, looking out onto the world that was one angel short. And what's worse is that nobody else seemed to notice that something important was missing. He had to carry that burden alone.

"Dean? What's going on? Are you all right?" Sam asked from his bed. Dean could hear movement as Sam sat up and shifted the blankets to the side.

"I don't know. I just saw something," Dean replied quietly, unsure as to why he couldn't seem to look away from the window.

"Uh, you saw what?"

Dean swallowed hard against the lump in his throat. "Cas."

Sam stood just behind Dean's shoulder. It hadn't escape his notice that his older brother hadn't been the same since returning from Purgatory.

"Cas? Where?"

"Right there… And…and," Dean said breathily, trying hard to focus and explain, "And earlier, on the road. I feel like I'm seeing him." He shook his head weakly, feeling worse as he admitted the truth.

"That's… not possible. I mean, you said it yourself. You made it out and he didn't, right?" Sam pointed out reasonably, trying to remain gentle with his obviously disconsolate brother. But he knew there was no point in being optimistic; Dean would respond best to hearing it from a realist.

"I tried so damn hard to get us the hell out of there." Dean finally turned away from the window, and fought the urge to look back. He didn't want to face the disappointment of that empty window.

"I know you did," Sam assured him, sighing softly.

Dean kept his back turned to Sam, not wanting him to witness the pain etched into his expression. Sam was patient, and he was honest (most of the time) but he couldn't reason Dean out of his slump this time. Dean knew Sam would try, and he knew it would be fruitless. Perhaps if he saw that Cas was dead with his own eyes, rather than as good as dead, then maybe that would have made all the difference. Maybe then his brother could pat him on the back and make it all go away, or at least help him forget for a while.

"You know, I could have pulled him out. I just don't understand why he didn't try harder."

Dean was remembering it all over again in perfect clarity. The way Castiel's hand slipped out of reach; the way he fell further downhill, defeated. Purgatory had drained the angel, weakened him beyond repair.

Dean remembered one night, a week or two before finding the portal, when they had stopped so Dean could rest. Dean had his back against a tree, and he shifted slightly, trying to make himself comfortable on the uneven terrain, and as he turned his head, he swore Castiel was asleep. The angel was sitting so still, his head dipped low, and Dean could see his back rise and fall as he breathed evenly. Dean had quickly turned his head back and closed his eyes, deciding not to whisper Castiel's name to see if he'd look up. Because if Castiel really was sleeping, then that meant he was even weaker than he had been letting on, and that terrified Dean.

At that point they had no idea how much further they had to go, and Dean had to contemplate the idea that maybe Cas wasn't strong enough to make it.

And his fears had rang true; because here he is without his angel.

"Dean…" Sam murmured and Dean turned to face him, but his eyes were trained on the window—he had to look. "You did everything you could."

"Yeah, but why do I feel like crap?" Dean's eyes were pleading, searching for an answer that would suffice, let alone take the misery away.

"Survivor's guilt?" Sam suggested.

"Hmm." Dean knew it was so much more than that. That was an answer he'd already tried on and decided didn't quite fit right.

"If you let it, this is gonna keep messing with you. You gotta to walk past it," Sam clapped Dean on the shoulder, giving him a purposeful look before walking past him into the bathroom.

Dean just stood there, lost. He didn't know what to do with himself anymore. Sleep had escaped him, no case could keep him preoccupied, and there was nothing he could do to bring Cas back. Benny had said so himself that there was no way to crack open the locked box that was Purgatory, and even if Dean could somehow do it, he knew he'd only be bringing back a corpse; assuming the leviathan left one behind at all.

Sam's advice was solid, but it was easier in theory than it was in practice, and for the remainder of the night, Dean lied awake, restless, still dreaming of his angel coming home.

That was of course, until the angel did in fact come home.

* * *

Since Dean was trying to come to terms with the fact that the energy was there to stay, he ignored it as it intensified to the point of making the hairs on his arms stand on end. It was more distracting and raw than ever but Dean tried not to give it any thought and for the first time, didn't look round.

He could hear Sam in the next room as he made coffee, completely oblivious to everything Dean was feeling. Again it bothered him how Sam seemed to be immune to… whatever this was, which implied that it was something Dean had invented for the sole purpose of, well, he wasn't sure what for. He didn't like to dwell on it for too long. Instead, he preferred to think of it as a strange, unexplainable phenomena that was purely of Castiel's doing—at least then Dean could comfortably say he had no control over it.

If he did in fact imagine it, then that meant he could, hypothetically, force it out of existence. If it truly wasn't real, then he had no excuse for still believing in it. That idea was as disquieting as it was unpleasant, and Dean found himself shunning it before it could take hold.

The false hope was like a security blanket that he needed just as much as he resented it.

But then he looked up from the sink and saw Castiel's reflection in the mirror, standing just beyond his shoulder. It was the same face he'd left behind at the portal, facial hair and all, but Castiel's gaze wasn't that of desperation, instead it was that of heavy burden. Almost like he didn't wish to be there.

Dean blinked in surprise and almost expected Cas to disappear in the half a second that his eyes were closed, but when he turned around, Cas was still there. He looked solid, real, too detailed to be a figment of Dean's imagination—even he, after all this time, couldn't remember Cas _that_ clearly. His memory could never do Castiel justice, as the angel was even greater standing there before him, filth and all.

"Hello, Dean," Castiel said, his voice thick and gruff. His eyes pierced Dean, boring into him with unapologetic composure.

Dean appraised Cas quickly, looking down the entire length of his 6 foot frame to see whether he was still all in one piece. It was hard to tell under that oversized coat and the loose mental hospital clothes, but from what Dean could see, Cas was completely unharmed. The leviathan hadn't managed to take a bite out of him, so that was something at least. Dean could work with that.

"Cas…" Dean breathed out, overwhelmed. He knew he must look ridiculous with his mouth agape and his eyes as big as saucers, but he couldn't stop staring. If he were to look away, Cas might just fly away, never to be seen again. That wasn't a risk Dean was willing to take.

Before Cas could say another word, Dean enveloped him in an overzealous hug that would have winded another human, but the angel seemed unbothered, with his arms still hanging at his sides. Dean buried his face into Castiel's shoulder, both hands gripping the material of his dirty coat. Secretly, he breathed the angel in. Since Cas never perspired, he still smelled the same; like honey and vanilla.

Dean didn't want to let go, but then Castiel's hands finally reached up and wrapped around Dean's back in a loose hug, and Dean had to pull back to keep himself from giving in to his instinctual urge to kiss the angel.

There were questions he needed answered before he could even consider the idea of holding Cas the way he wanted. For one thing, how was Cas even alive? More importantly, was Cas actually even Cas at all?

"How are you—" Dean started but then Sam knocked on the bathroom door.

"Sam," Cas responded, and then Dean's brother burst in through the door, his brow furrowed in disbelief. But yes, it was Castiel that had spoken, he hadn't just misheard.

Dean covertly wished he'd had more time to have Castiel to himself; time to say everything that had been eating at him since escaping Purgatory. He wanted Cas to know that it had never been his intention to leave him behind. He wanted to ask why Cas couldn't fight just that little bit harder when he needed to. Dean needed to know that Cas didn't resent him for everything that had happened.

But Sam didn't know what had happened that fateful day, didn't know why Dean's guilt was greater than it should be. And Dean was far too ashamed to have his brother know it now, or ever.

Sam dragged Castiel out of the bathroom and sat him down, offering him food or drink as he paced back and forth, flustered; forgetting that Cas was an angel that didn't need neither food nor drink. Dean reminded him of that fact in a quiet mumble and stood aside, leaning awkwardly against the wall as his brother took the remaining seat.

Already, Dean had distanced himself from them and the situation, not wishing to face the guilt that was personified in the man wearing the trench coat. He thought that perhaps he had mistaken that look in the mirror for heavy burden when it was actually controlled rage.

The angel blamed Dean, and rightfully so.

And that blame had Dean lost for words.

* * *

Dean wanted to understand. He really did. But Castiel's non-explanation didn't sit well in his gut, and his imagination filled in the missing gaps of the story with worse case scenarios in which Cas would wind up hurt, dead, or worse. Because nothing good came this easily or without consequence, and Dean was putting up his walls in preparation for something awful to try and tear them down.

Someone or something had brought Cas back, and Dean doubted it was out of the kindness of their or its heart. No favour was given without expecting something in return, something that seemed a bigger sacrifice than what the favour was worth. So while Dean wished he could just enjoy Castiel's return and be done with it, he just couldn't. He couldn't hold the man in his arms and run off into the sunset, because there would be something sinister waiting for them there.

Getting Castiel back could only end in grief, but Dean still couldn't help getting reattached—after all, this was what he had wanted for all these weeks.

And the moment Cas stepped out of that bathroom wearing his usual suit and tie, and a clean coat, his face shaven and hair pushed back effortlessly, Dean almost forgot all that. Which just made everything harder; quite literally in fact, as Dean shifted subtly in his seat, trying not to draw attention to the growing bulge in his jeans.

Cas just looked like the best version of himself, which Dean hadn't seen in a long time since something always seemed to get in the way: whether that be Castiel's vessel falling apart from the leviathan writhing inside him, or dazed and drowning in hospital clothes that were almost two sizes too big, to being covered in filth and with overgrown hair in Purgatory.

Now Dean was struck by how _attractive_ Cas really was, even while still wearing at least three layers of clothes. And what's more is that Castiel had no idea just how good-looking he was despite being told numerous times by various people. That humble ignorance did nothing but add to Dean's desire, and made him want nothing more than to dirty his clean angel—a craving he didn't dare mention to anyone, least of all Cas.

He knew these were dangerous fantasies to have, considering Castiel was his best friend, and an angel. But now it was all the more complicated by this mysterious return from Purgatory that all logic dictated shouldn't even be possible. Something was very wrong, so Dean didn't kiss Castiel despite once again wanting to. It just wasn't the right time.

It was _never_ the right time.

* * *

When Castiel never brought up what happened at that portal, Dean's guilt grew out of control. It sent his imagination into overdrive, and he assumed the worst for what Cas must think of him. Dean didn't want it to be confirmed that he was a failure of a friend; that he let down those who depended on him most, and worse still, that he hadn't tried to find a way back to him.

Not hearing any of it said aloud set Dean's teeth on edge, and his shoulders sat in a permanent state of tension as though coiled at all times in anticipation for the accusations yet to come. And he still hadn't decided what he ought to say for when they did.

He knew he should say sorry, though sorry, in his mind, would never be enough. He knew he should probably try his best to explain himself, but he didn't know how since he hadn't chosen to let go in the first place, and he hadn't spent a day since not hating himself despite trying his best at the time. He thought maybe he could just focus on how happy he was to have Cas back, but he knew that it would sound forced, never mind just how strongly he really meant it. Cas would see right through the distraction and think: you're happy to have me back but that doesn't change having been left behind in the first place.

Eventually the waiting grew to be too much, and Dean's uncertainty on what he should say shifted into what he knew was probably very misdirected rage. He didn't know how to say sorry or how to explain himself because he really hadn't done anything wrong. If he had, then he'd be able to move on with the knowledge (no matter how awful) that it was his fault. At least then he'd have a reason why. But this? No, this was on Castiel.

Cas had been weak, and swiftly losing more and more strength as the time passed, and he had said nothing.

Cas had given up hope before the battle had truly begun.

Cas hadn't tried hard enough to hold onto the hand Dean had held out even after the portal had already closed between them.

Cas had expressed time and time again his doubts of an angel being able to pass through the portal meant only for the escape of human souls. He'd decided long before they'd found it that he wouldn't be able to follow the hunter to freedom on the other side.

Dean couldn't take it anymore, and decided that if Castiel wouldn't put up the good fight, then he would. But when he confronted the angel, he got a response he never expected to hear: _"so you think this was your fault?"_

Even Dean's accusations fell back on him, revealing the self-loathing he felt within; expressing how, in the end, Dean still blamed himself. Sure, he had done everything to get Castiel out, but it hadn't been enough, and Dean simply couldn't forgive himself for that. But apparently Castiel didn't need to. It sounded like he had nothing to forgive Dean for, but how could that be?

And Dean didn't find out for what seemed like the longest time, but when he did, he wished he had never found out at all.

* * *

"That was a bonehead move back there. You could have gotten yourself killed. Why didn't you wait for me?" Dean slammed the trunk of the Impala shut, struggling to contain himself, though he managed to censor out any and all swearwords he wanted to use.

"Well, I didn't get killed. And it worked," Cas muttered dully, glancing briefly in Dean's direction.

"And if it didn't?"

"It would have been my problem."

Dean couldn't believe that Cas would have the audacity to say such a thing, not after everything they'd been through together.

"Well, that's not the way I see it," Dean retorted sourly.

Cas turned to face him. "Hey, everything isn't your responsibility. Getting me out of Purgatory wasn't your responsibility."

"You didn't get out. So whose fault is it?" Dean was still waiting for the allegations to come, still expecting Cas to turn on him. In a way, Dean kind of wanted him to. He wanted it over and done with.

"It's not about fault. It's about will. Dean, do you really not remember?" Castiel tilted his head slightly to the side, his eyes searching Dean's imploringly. Dean suddenly felt uncomfortable, like Cas was able to see right through him to his very soul. Who knew if all that angelic crap allowed him to do that?

Dean scoffed, livid with disbelief. Did he really not remember? Cas was either rubbing the blame into Dean's face, or he really didn't know just how much he mattered to the hunter, or just how much he had been missed.

"I lived it, Cas. Okay, I know what happened."

"No. No, you think you know. You remembered it the way you needed to." Castiel cast his eyes to the ground, as if he felt ashamed of Dean, or rather, of what he'd made Dean feel.

"Look, I don't need to feel like hell for failing you, okay? For failing you like I've failed every other godforsaken thing that I care about! I don't need it!" Dean stepped closer to the angel, clenching his hands into fists to keep himself from reaching up, grabbing Castiel's coat, and shaking him.

"Dean. Just look at it," Cas reached out his hand, tentatively touching his fingers to Dean's forehead, ignoring the hunter as he instinctively flinched. "Really look at it."

Dean knew he should be used to all of Castiel's mind tricks; being touched between the eyes or on the shoulder and appearing somewhere else without feeling much of anything aside from a little nausea, being sent back in time which left his insides in a state of shock for a week or two at a time, or reliving the exact details of a memory. He should be used to it; after all, Castiel was prone to using his powers without first thinking of asking permission or giving some forewarning, but Dean, this time, recoiled from Castiel's touch without knowing why.

This time his instincts insisted he look away from what the angel wanted him to see.

 _"_ _Cas! Damn it! Come on!" Dean stepped into the portal, noticing that the edges were caving in on themselves and the hole was rapidly shrinking in size as it sensed now that the only human soul in Purgatory was now enveloped in its light. The portal was leaving Castiel behind. Dean desperately reached his hand out, urging Cas to battle on despite what Dean thought was his dwindling strength. "Come on! I got you! Hold on!"_

 _"_ _Dean!" Cas called out to him, but he wasn't allowing Dean to pull him forward. In fact, it felt more like he was pulling back._

 _"_ _Hold on!" Dean shouted, almost begging._

 _"_ _Dean!" Cas gave Dean's hand one final squeeze and pushed it away, staring up at Dean's bewildered face before sternly demanding him to go._

 _Dean didn't want to believe it, and he_ _ **couldn't**_ _believe it, but before he could do anything the portal finally collapsed and Cas was suddenly long gone—thought never to be seen again._

Dean was abruptly pulled back to reality and he felt a weakness in his knees like they couldn't be trusted to keep him standing upright. He hesitated to look Castiel in the eye, afraid now of what he might do or say because everything seemed both right and wrong all at once. Kissing Cas seemed appropriate, and necessary, but also forbidden somehow—like Dean would be crossing an important line were he to pull Cas in and feel his lips against his own.

"See it wasn't that I was weak. I was stronger than you. I pulled away. Nothing you could have done would have saved me, because I didn't want to be saved." Castiel admitted.

Dean blinked, refusing to accept what he was hearing. "What the hell are you talking about?"

"It's where I belonged. I needed to do penance. After the things I did on Earth and in Heaven, I didn't deserve to be out. And I saw that clearly when I was there. I planned to stay all along. I just didn't know how to tell you… You can't save everyone, my friend, though you try."

Dean's eyes brimmed with unshed tears, his mind reeling from what he had just seen. Or rather what he just saw for the second time. He wished Castiel hadn't shown him the truth, because the idea of failing to save the angel was less painful to him than the idea that Cas didn't want to be saved. This meant he could still lose Castiel. They weren't out of the woods yet.

And thinking back, Dean realised he had seen it coming all along. All the times Cas had voiced his doubts on being able to pass through the portal, and the times he suggested that maybe there wasn't such a portal to begin with. Cas had been trying to tell him all along not to get his hopes up, because he knew from the very beginning he wasn't going to get out.

When Castiel had stopped Dean and said; _"thank you. For everything,"_ he was actually saying goodbye. The signs had always been there, but Dean had turned his back time and time again, refusing to listen, refusing to see what was so very clear. He hadn't been ready to say goodbye then, and he still wasn't ready to say goodbye now.

This wasn't the end, and Dean wasn't about to let the angel disappear from his life after fate had brought him back.

Dean wanted Cas to understand that they had both made mistakes, had both done things that got them here, and Cas didn't have to punish himself for it. He didn't have to die to make up for all that he had done. Dean wanted to embrace him and make him swear that he would never again sacrifice himself for the sake of Heaven or for Dean, because no amount of bad could ever outdo the good, and nothing could stop Dean from wanting Castiel.

"Hey, everything okay?" Sam asked, approaching them both warily. He saw too late that he had interrupted something.

"Yeah. Just, uh, setting a few things straight." Cas replied quickly, once again standing to attention, sweeping the dense conversation under the rug as if it had never happened.

Dean was still shell-shocked, and he briefly mulled over all the words that hadn't passed his lips, and he swallowed them back, thinking it was best to keep them for another day. What he didn't realise, was that that day would never come.


	3. The Third Time

The third time Dean wanted to kiss Castiel was when the angel admitted he wanted to die. Dean had heard the self-sacrifice, self-loathing spiel before, numerous times in fact, but it never got any easier to listen to. And he never imagined the extent of Castiel's demise into what could only be described as a deep depression. Cas, like Dean himself, had a habit of suppressing his pain and masking it behind a façade of impenetrable bravado; though he was more subtle; more controlled, about it.

Dean had witnessed Cas survive against the odds time and time again, sometimes outright bad-assing his way out of a tough situation. So it easy to forget sometimes that Cas wasn't invulnerable. He could be hurt, or killed. Just one false move and an angel blade could slide between his ribs, or pierce through his heart. Dean wasn't a stranger to angel deaths; the whole bright flash of fading grace and the dark shadow of wings permanently burnt onto the ground. But he still couldn't picture Castiel's lifeless body in another angel's place.

Dean thought idly that perhaps he had been spoiled in that whenever Cas disappeared, he always came back. Hell, he'd watched Castiel explode at the snap of Lucifer's fingers and still come back all in one piece. Cas was the only reassurance he had that God was still around, or that he even really existed in the first place.

It was this that blurred Castiel's vulnerability.

Though Dean realised much later on that, once again, he had turned his back on what was right in front of him. He had shut his eyes to what he hadn't wanted to see. Because when it came to Cas, he preferred to create a lie to protect himself from the harsh truth. Dean liked to think of his angel as this all powerful thing that he had no reason to fear losing, but in reality, that simply wasn't the case.

The more time Cas spent on Earth, the more he came to resemble a man; a man with all the weaknesses and flaws that Dean himself had—being human. The changes were so gradual that they were easy to ignore unless you knew Cas well enough; which Dean certainly did.

Dean saw how the angel sometimes walked with less poise; his shoulders slumping out of their usual sharp arch, and he tended to fidget more as though he were bored; though Cas often argued that he was more patient with time than most. And Castiel sometimes seemed as if he was starting to lose interest in certain aspects of human life as it became commonplace for him. Cas was losing focus and was easily distracted at even the worst of times, and Dean often bit his tongue to keep himself from urging the angel to take more care of himself.

It hardly seemed appropriate for him to ask that of an angel when he, a mortal man, lived a life of danger and eventual peril. Dean couldn't expect Cas to take the warning in stride and actually act upon it when he was sure not to follow the same advice if it was given to him.

Dean was starting to consider this more since Cas had stayed behind in Purgatory. He thought how Cas _wasn't_ some indestructible creature, he was a person; a person whose torment actually involved more than physical scars. Cas could _feel_. And after everything that had happened over the past few years, he was becoming well acquainted with guilt and regret and sorrow and loss. More than Dean really expected, but as he came to see it more in the angel, he could relate.

He understood better than anyone.

He had found it strange when Cas suddenly announced that he was going to become a hunter, looking between the two brothers with a gratified smile. It wasn't unusual for Cas to spend time with them, and Dean appreciated his company, and even yearned for it whenever he was gone, but Cas hadn't really set out on a hunt with them before without being asked. Neither Sam nor Dean wanted to bother the angel with their problems though they still seemed to do so all the same, which was why they didn't always call upon him even when Cas was sure to help them get the job done a whole lot quicker. So they certainly never expected him to make his presence permanent, though Dean figured that Cas turning off angel radio had something to do with it.

Or everything to do with it.

Dean was a little taken aback when Cas told him that he no longer wanted anything to do with Heaven, though he knew it made a lot of sense. Heaven was surely a mess, and Cas was probably not welcome back to help clean it up. It just startled him to hear it said so plainly and upfront like that. And Dean had known then that it wasn't as simple as Cas made it out to be. There was pain in Castiel's actions, and Dean knew that though the angel hid it well.

But Dean hadn't known just how complicated it truly was.

And he knew he should have asked. He should have probed with more questions, maybe even try to console Cas and offer advice, even if the only guidance he could give was utter rubbish and totally useless in the grand scheme of things. Maybe then Cas might have reconsidered and gone to face his anxieties head on.

But the truth was that Dean hadn't wanted Cas to go.

Secretly, the idea of Cas staying with him for any longer period of time thrilled him. It meant Cas would be there at least for a few days, if not longer, and the strange energy that always surrounded him would be there too.

Which was why Dean wouldn't let Cas zap away on his own, making him endure the long car ride though Cas had commented numerous times that that method of travelling was slow. While Sam was perfectly good company, Dean liked the idea of having Cas sit in the back seat and hearing all his unusual commentary on the journey. He hadn't wanted to give up his chance to spend more time with his angel, and he had known that Cas would feel obligated to meet Dean's request not to fly off and leave them behind.

He hadn't been able to help but glance at Cas in his rear view mirror, watching as the angel sat quietly with his hands clasped together on his knees. Cas was only this quiet when he thought nobody would notice, and for once Dean saw just how lost he really looked. Cas had stared at his hands, eventually wringing them together in what Dean assumed was misery, but still, Dean didn't ask questions.

While the three of them worked the case, Cas seemed eager to help, but the angel had a very lateral way of thinking that didn't comply with social normality. Which, though amusing, was difficult to follow. Though Dean wouldn't have it any other way if it meant Cas would leave. He liked to think that Castiel was coming to enjoy the experience as he learned more about what he and Sam spent their days doing. Maybe the hunt was the distraction Cas needed.

But whenever Cas thought Dean wasn't looking, he'd shy away and fall behind, waiting and hoping to be called upon, but he never sought out an escape from them. Cas was there every step of the way, which in itself was unusual. Dean had been worried; sensing the false bravado more and more as the time passed until eventually he couldn't hold his tongue any longer.

"Your father… Beautiful handwriting," Cas murmured gently, sitting on the edge of the bed with John's journal held carefully in his hands. He turned each page delicately, taking great caution with it as he inspected the contents. Dean hadn't minded when Cas had picked it up to read, in fact he felt an unexpected pleasure in Castiel's sudden interest in Dean's world.

Dean glanced over at the angel and frowned, seeing the heaviness in Castiel's posture and in his expression. Cas wasn't reading to pass the time, he was trying to drown himself in something other than his own thoughts.

"How you feeling Cas?" Dean was relieved to finally be asking, though now he was worried at the possible response.

"I'm fine," Cas replied, his tone dismissive.

"Well, I just… I know that when I got puked out of Purgatory, it took me a few weeks to find my sea legs," Dean continued, urging Cas to open up to the truth; the same truth that Dean hadn't been ready to hear.

"I'm fine," Cas reiterated.

This was going to be as difficult as Dean had expected. "Don't get me wrong, I'm happy you're back. I'm freaking thrilled. It's just this whole mysterious resurrection thing, it always has one mother of a downside."

Castiel closed the journal, grudgingly turning his full attention to Dean. "So, what do you want me to do?"

"Maybe take a trip upstairs," Dean suggested. Castiel hadn't been the same since he came back from Purgatory, and while Dean was still concerned as to who or what brought Cas back, he thought that maybe Cas turning off angel radio was more important. Cas had been trying to work the case in the hopes that he'd help where he could—where he was allowed to—but he couldn't exchange his brothers and sisters for the people down on Earth. Healing one didn't heal the other.

Though Dean didn't really believe that the angels deserved the help after all that they had done. He assumed Cas resented their actions as well, but the angel would always feel obligated to try to change them wherever he could. Castiel always saw hope for his own kind.

"To heaven?" Cas asked, incredulous.

"Yeah. Poke around, see if the God squad can't tell us how you got out."

"No," Cas said immediately, looking away.

"Look, man, I… I hate those flying-ass monkeys just as much as you do, but—"

"Dean! I said no!" Cas interrupted firmly, his voice rising above Dean's and startling the hunter.

Dean realised that he had hit a nerve. He watched as Cas tried to hold himself together and reel in the pain he had accidentally let out and Dean recognised the struggle. It hurt him to see Cas like this, and he was reminded of how the angel had pushed Dean's hand away at the portal, wishing to stay, suffer, and die, the way he thought he deserved. Dean would never believe that Castiel could earn such a severe punishment, and he wasn't about to let Cas leave him again.

Dean got up from his seat and moved to sit across from Cas, wishing he could instead sit at his side and pull the angel into his arms. He wanted to embrace him; wanted to feel Castiel's face nuzzle into the crook of his neck. He thought about burying his nose and lips into Cas' hair, his hands lazily trailing up and down the length of Cas' arms as he comforted him. He knew he'd never know the right words to say, but he hoped that his kisses could say what he needed Cas to know.

He hoped his kisses could tell Castiel that he never wanted him to go.

Instead, he said; "Talk to me."

"Dean, I—" Cas was quiet as he set the journal aside, shifting so he was leaning forward more towards Dean. "When I was… bad… and had all those things—the leviathans, writhing inside me, I caused a lot of suffering on Earth, but I devastated Heaven. I vaporized thousands of my own kind, and I… I can't go back."

Dean's heart sunk in his chest, knowing he should have asked Castiel sooner. His fear of losing the angel had stopped him from giving what Cas needed: his help. And now he hated himself for it.

"'Cause if you do, the angels will kill you," Dean said.

"Because if I see what Heaven's become, what I… what I made of it… I'm afraid I might kill myself."

Dean stared into the face of this broken man and the need to hold him grew. He couldn't find the right words because there simply weren't any. Cas gazed back at him, his blue eyes wide and tainted with grief and Dean just blinked, overwhelmed, his hands inching forward to try and reach out and touch Cas. He thought maybe he could entwine their fingers, give Castiel's hand a tight squeeze that said that he wasn't going to allow him to let go this time. He would never let the angel die; he couldn't.

He couldn't imagine another day devastated over losing his Castiel.

"Hey," Sam greeted as he came in through the door. Dean's hands slid back and balled into fists on his knees. He hadn't taken the chance to hold Castiel the way he wanted to, his lips hadn't kissed Castiel's in a promise to be there, and he hadn't saved his angel from his pain.

He silently swore not to let the opportunity pass him by again.


	4. The Fourth Time

The fourth time Dean wanted to kiss Castiel was when he had watched a reaper murder the former angel right in front of his eyes.

While he and Sam were out looking for Castiel, Dean was awfully distressed. More so as the hours passed with little hope of finding him in time. There was a trail to follow; people who recalled seeing a man that matched Castiel's description, which assured Dean that, for the moment, Cas was still on the move. But every trail had an end, and Dean thought that maybe he wouldn't like whatever he found there; assuming they ever actually found it at all.

What was he to think if suddenly they hit a dead end and all the evidence of Castiel's continued existence just stopped?

When would he know to stop looking if that happened? Could he in fact stop looking at all if it truly came down to that? He really wasn't sure if that were even possible. Had he had a way of going back to Purgatory when the angel stayed behind, he would have taken it without question. Castiel mattered to him, even more than he ever let on. And while there would be a life still there without the angel in it, Dean had decided that that wasn't a life he wanted to live if he could avoid it.

But there was something else he worried about too. He had to wonder if Cas even really wanted to survive this in the first place. After all, the man tended to suffer under his own self-deprecation, and torment himself so completely over any mistakes he made; big or small. He had sacrificed himself in Purgatory for the devastation he had caused in Heaven, and he had wanted to kill himself upon being brought back to Earth, and Dean doubted that his mind had really changed since.

Something as serious as that didn't just simply go away on its own, though he always hoped that maybe, just this once, it could be that simple.

It didn't help that Castiel was getting better at hiding it; masking it behind a stern expression and keeping himself occupied as if there wasn't this heavy depression weighing him down like wading into the ocean with stones in his pockets.

Dean knew that this time wouldn't be any different, unless it was somehow worse. The angels falling was a tragedy; the mess of Heaven pummelling down onto Earth, and there didn't seem to be any resolution in sight. How does one go about fixing something like that? And Castiel surely felt helpless with his grace stolen and his body now that of a mortal man. What could Cas do? Dean certainly didn't have any ideas to offer, and nor did he have the ability to comfort the now former angel they way he needed and deserved.

Dean had nothing. But he decided to start with making sure Castiel was safe.

There were angels hunting Castiel down, enraged at what he had inadvertently done, and their desire for revenge was palpable. But it could never outweigh Dean's desire to save him. The hunter would gladly take on any angel that dared to cross him, and he wouldn't hesitate to gank any of those now wingless sons-of-bitches that wanted to take his Castiel away.

Castiel deserved to live, even if he didn't believe it.

* * *

Dean's fears rang true and when he and Sam burst in through the door to see Castiel tied to a chair, his torso littered with fresh wounds from being tortured. There was a look in the man's eyes: the look of fear, but also that of acceptance, as though he was preparing himself to die. Maybe a part of him even wanted it. Seeing Cas like that broke Dean.

"Cas!" Dean shouted, watching helplessly as the reaper stabbed Castiel in the stomach.

Dean wasn't sure what came first; the grief or the rage. It was both together that propelled him into action though all he could get from it was revenge—which would never make up for the loss. He whipped the angel blade out, his jaw clenched and his eyes manic with the need to kill this bitch for what she had done. As he ran forward to strike her down, he was thrown across the room with just a swish of her hand and his back hit the wall, disorientating him and everything seemed to move in a fast blur. He saw his brother being thrown forward into the wardrobe and the reaper's back as she moved in on him. Dean tried to gather himself and he edged around the chair, eyeing the blade still protruding from Castiel's corpse. His heart panged at the sight of Cas' still body, his chest unmoving with all the air taken away from him.

But now Dean had to save his brother. He didn't have the time to stop and mourn.

He couldn't watch as he pulled the blade from Castiel's body, but he saw the blood coating the metal as he gripped the handle tightly in his hand. The sight of it made everything real, somehow, and his own life no longer seemed to matter anymore.

Now it was just about Sam.

As the reaper turned around, he struck her hard with the blade, piercing it straight through her, his expression severe and unapologetic as he watched her eyes glow and then fade as the life left her. Then he turned to Castiel, his heart broken as he hopelessly said his name and crouched in front of him, one hand reaching for his shoulder and the other grasping his knee. But there was nothing.

He moved and held Castiel's face in his hands, caressing his cheeks, but all he felt was a body slowly turning cold.

"Cas!" his voice quivered and his eyes started to brim with unshed tears, wishing he was wrong; wishing there was still somehow a chance. He had already lost so much, and now he had lost the man he loved. But he still wasn't ready to say good bye, and he doubted he ever would be. He just didn't know where to go from here or what to do. His hands slipped away from Castiel's face, hovering for a moment by his chest, wanting to hold the material of his shirt: wanting desperately to hold onto him.

Dean looked to Sam, his eyes big and lost. Sam was all he had left. "Sam, he's gone."

It still didn't sound real to his own ears, but it felt horrible and true on his tongue. It had been what he feared he might one day say after Castiel admitted his suicidal thoughts to him.

When Sam had nothing to say, Dean looked at him again and realised that Sam wasn't carrying himself the way Sam normally did. This was Ezekiel taking the reins of Sam's body. At that he nearly begged, desperate for the angel to do something, but the words never passed Dean's lips. They didn't need to. Somehow Ezekiel knew that Dean needed Castiel back; he could see the love Dean held for the former angel.

Dean watched the angel kneel beside Castiel and reach out, healing his wounds with power permeating his palm with a bright light. Could Castiel really be saved?

Ezekiel stumbled backwards, his body weakened by the strain of using his already weakened grace, and he collapsed against the wall. Dean was startled, worried about his brother and whether his health was now in jeopardy if Ezekiel wasn't strong enough to continue healing him.

"Dean?" Castiel asked. Dean froze for a second, unwilling to believe just yet that Cas was truly alive. He didn't want to find that his hope was wasted. Turning around, he saw the bright blue of Castiel's eyes.

"Hey…hey," Dean placed his hand on Castiel's knee, relief flooding through him to see Castiel's eyes boring into his.

"And Sam…" Cas glanced over at the younger Winchester.

"Cas? You're okay?" Sam sounded confused as he tried to understand what he had missed.

Dean slowly stood upright, his heart still hammering in his chest and his hands were shaking. He was still trying to wrap his head around losing Castiel and then getting him back. It seemed he was right in thinking that he was spoiled in somehow having Cas find a way back to him each time he was taken away

There was so much he wanted to say, and so much he just didn't have the right words for. He wanted to tell him he loved him, and how he couldn't ever thrive in a world without him in it. He wanted to hold Castiel's face in his hands again but this time brush his thumb over Castiel's lips before kissing him.

But instead he looked at him, his eyes hard and his jaw once again tensed, and said; "never do that again!"

Castiel gazed up at him, his brow furrowed both in confusion and in surprise. "Alright," he agreed in a daze.

Dean hadn't kept Castiel safe. His desire to just didn't matter because in the end it was Ezekiel that saved him. It was just god damn luck and coincidence, and Dean couldn't just rely on that in future.

Because there would come a day when luck wasn't on his side.

* * *

Thanks for reading, guys! Just one more chapter to go (Though I think it will be a short one). I've started working on another story that I'm very excited about and I think you might really enjoy. So I'll hopefully start uploading chapters of that one soon. Keep an eye out for it :D


	5. The Fifth and Final Time

The fifth time Dean wanted to kiss Castiel was when he goodbye for the last time.

Dean always knew that the end would come for him long before his time; that his soul would pass and leave behind a body still in its prime. He knew that there would never come a day when he could sit on his porch and stare out across his lawn, his hair grey and his bones tired and weak with age. He wouldn't have the chance to have a life outside this one where he and his brother journeyed the country to save the world from monsters.

And he had come to accept it.

There wasn't fear in knowing he would die—there was only fear in how it would feel when it happened.

He had died before when the hellhounds came to drag his soul to hell, and he remembered their claws tearing into his flesh and cracking his ribs open as they mauled him to death. It had been agony. It had happened so fast, but the pain was inconceivable, and Dean hadn't been able to accurately describe it since.

It was the major details that somehow continued to evade him: like what it felt like at the exact moment he died.

He still didn't know.

And then he had died again when Metatron stabbed him. There was pain then too, but the life drained from him slowly and he just felt empty somehow. He thought that maybe his body had been in shock—which would explain feeling numb—but it was saying goodbye to Sam that was the worst. He remembered Sam's arms holding him up and half carrying him across the room, and he remembered losing mobility in his legs as he slowly died. Dean remembered how it was so different from the first time: most likely because of the mark of Cain.

But again he didn't remember feeling the moment he actually passed.

He supposed it was the same as falling asleep. You never really knew when reality became dreams though you knew the difference when you woke up. If he had to describe dying—actually dying—then that was the analogy he would use.

But it was why he was so scared now.

Scared because maybe this time he would actually feel it. History dictated otherwise, but that didn't stop him from thinking: _what if?_ What if fate knew this was truly the end and he didn't miss it this time? And he would have to feel it alone without his brother or Cas at his side. He had to be ready, and he had already accepted it, but that didn't dispel the fear.

And it didn't make saying goodbye any easier.

There were things he knew he needed to say; he could feel the words on the tip of his tongue, yet he was still unsure as to what they were or what they meant or if they were things his brother and his best friend wanted to hear. Then there were the things he just didn't need to say aloud—they knew them already, and they understood. But he knew that as soon as he left to face Amara on his own, he would wish he had said them again anyway. Because what if they weren't the things they thought about and remembered after he was gone? What if they forgot just how much he cared?

But then Dean reasoned that he'd think that anyway, no matter what he said now. It was the heart part of him that wanted to stay, and was just looking for a reason to. One that outweighed the reason why he had to sacrifice himself. His mind knew, however, that there was a right here and there was a wrong: dying with his family rather than dying to save them—there was no question of which was which. They had lives ahead of them, and Sam still had that hope of growing old the way Dean knew he himself never would. And Cas deserved to live no matter if the angel thought otherwise, and Dean expected him to lead a life of free will and peace. There had to come a day when Castiel no longer missed Heaven; a day when the angel knew for certain that Earth was his home and the Winchesters were all the family he needed.

Dean knew that Cas would want to make his death mean something. He knew Cas would live on in his name. And that was almost comfort enough.

But it still didn't make saying goodbye any easier.

"Dean…" Castiel's eyes were grave as he gazed upon Dean for what the hunter knew was the last time. And Dean realised that even in death he would miss those piercing blue eyes.

"Cas," Dean breathed, the faintest hint of a sad smile tugging at his lips.

Castiel pulled him into a tight embrace and Dean melted in his arms, breathing in the scent of his coat and feeling the material beneath his hands. It was tempting to just hold on and never let go. Like he could pretend for a few moments longer that the world wasn't ending—or at least _his_ world. He wanted more time to pretend that he still had a future where he could say and do all the things he wanted but never allowed himself to.

Dean was dangerously close to backing out now, and nearly gave into it when Castiel didn't let him go.

"Okay… okay," Dean murmured, smiling at first with a wet shine to his eyes of threatening tears, then his face fell. "Alright…"

Castiel was squeezing him so tight; and Dean could actually feel his arms shaking beneath the baggy sleeves of his coat. His fingers were trembling on Dean's back and the hunter near promised he would stay. He was so close.

Then Castiel let him go, staring at him with agonized eyes but the posture of a deflated soldier—always trying to stand tall and fight for what was right, or good, or significant: and Dean still couldn't believe that Cas seemed to think of him as all three. And he could never thank him enough for all he had done. Couldn't put into words what his life had become since Castiel walked into it; quite literally in that shack all those years ago. Sparks flying and surrounding him symbolically in light.

If only he had known then all that he knew now. Maybe then he could have lived his life the way he always wanted to: with Castiel.

Maybe if he had kissed him sooner or held him longer… maybe then they wouldn't be here saying goodbye for the last time. And a part of him wanted to do it all now and just hope it wasn't too late. He thought about caressing Cas' cheek in the palm of his hand, leaning in close and kissing him gentle and soft and sad, but loving too.

"I could go with you," Castiel offered quietly, stricken at letting Dean die alone. And that was Cas: always ready to give everything he had, but Dean couldn't dare be selfish enough to take it.

He wanted to kiss Castiel, but, with his hand having already reached out slightly, Dean retreated. His hand hesitated, and then withdraw, his heart heavy and burdened and lost because he couldn't kiss him the way he wanted. If he did, there was no way Cas would let him go. The angel would find a way to die at his side. And Dean would not let that happen.

"No, no… No," Dean answered, "No, I got to do this alone." He had to give Cas reason to stay; and not just now, but for all the years to come. He didn't want the angel to one day stop and let the world continue on without him. "Listen, if—when—when this works, Sam… he's gonna be a mess. So look out for him, okay? Make sure he doesn't do anything stupid."

Cas needed to promise him.

"Of course," Castiel vowed, and Dean could see he meant it. Cas was going to grant him his dying wish to not just look out for his little brother, but also to stay alive. Dean couldn't kiss him, but something told him he didn't need to: Castiel knew, and the angel wanted to kiss him too, but didn't for all the same reasons.

Dean placed his hand on Castiel's shoulder and gave it a squeeze, gazing into his eyes, "Thank you. For everything."

It was what Castiel had said in Purgatory when he was really trying to say goodbye without having to utter the words. Because goodbye wasn't for them. All this time, they always found a way back to one another, and though they knew it was different this time, neither of them dared say it was the end.

And suddenly Dean wasn't so afraid anymore.

 _'_ _Thank you. For everything';_ was their ' _goodbye'_ , and their ' _I love you'_.

* * *

Thanks so much for reading, guys! I'll admit, I really started to struggle by the end haha. But I'm glad I finished and I hoped you liked it. Keep your eyes peeled for my next Destiel story called The Road Trip! Should be ready to start uploading it soon, and I think you'll really enjoy it.


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